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Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity
University of Athens, Department of Pharmacy, Division of Pharmacognosy and Chemistry of Natural Products, Panepistimiopolis Zografou, Athens 157 71, Greece
Kenya Medical Research Institute, Centre for Traditional Medicine and Drug Research, P.O Box 54840, Nairobi, Kenya
ISOMer, Laboratoire de Pharmacogénomique Marine, Faculté de Pharmacie, 1 Rue Gaston Veil, F-44035 Nantes, France
* Author to whom correspondence should be addressed.
Received: 7 April 2007; in revised form: 12 May 2007 / Accepted: 14 May 2007 / Published: 15 May 2007
Abstract: Three new pentacyclic triterpenoids: (20R)-3-oxolupan-30-al (1), (20S)-3-oxolupan-30-al (2) and (20R)-28-hydroxylupen-30-al-3-one (3), along with (20S)-3β-hydroxylupan-30-al (4), the latter previously described as a constituent of an epimeric mixture, were isolated from Acacia mellifera. In addition, the known metabolites 30-hydroxylup-20-(29)-en-3-one (5), 30-hydroxylup-20-(29)-en-3β-ol (6), atranorin, methyl 2,4-dihydroxy-3,6 dimethyl benzoate, sitosterol-3β-O-glucoside and linoleic acid were found in the analyzed plant species for the first time. The structures of the new metabolites were elucidated by extensive spectroscopic analyses and their relative stereochemistry was determined by NOESY experiments. The new metabolite 3 exhibited significant cytotoxic activity against the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma.
Keywords: Acacia mellifera; lupanes; cytotoxicity; NSCLC-N6 cell line; (20R)-28-hydroxylupen-30-al-3-one; (20R)-3-oxolupan-30-al; (20S)-3-oxolupan-30-al
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Mutai, C.; Abatis, D.; Vagias, C.; Moreau, D.; Roussakis, C.; Roussis, V. Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity. Molecules 2007, 12, 1035-1044.
Mutai C, Abatis D, Vagias C, Moreau D, Roussakis C, Roussis V. Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity. Molecules. 2007; 12(5):1035-1044.
Mutai, Charles; Abatis, Dennis; Vagias, Constantinos; Moreau, Dimitri; Roussakis, Christos; Roussis, Vassilios. 2007. "Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity." Molecules 12, no. 5: 1035-1044.